I have completed my engineer degree (in computer science) and then applied for two master degrees in computer science (same university, different faculties and different specializations - artificial intelligence vs information system engineering).
This semester I'm going to defend first one and next semester second one. I am seldom asked on interviews hearing question "why are You studying two same degrees?" and I was always truthfully answering that "because I'm interested in them plus they are different fields in IT". In most cases it ends with impression like "that's cool... but weird". Up to this point I have never had problem with any jobs, so I just was ignoring that and continued with it.
After acquiring master degrees I want to stay in one of those faculties for PhD, but I don't want to stay in university after this.
Up to this point, my plan is pretty clear.
However, during past work I had opportunity to lead small group of programmers and right now I have formed something like "private student club" (about 30 active people) and we are doing two cool projects for nearly year and it's going great. I lead them all and actually I think I like it. By "I think I like it" I mean, that I have spent many hours on crawling through Internet and searching for management techniques and applying them. I have an idea of starting studying management (as parallel studies to PhD of CS).
In the mean time, for 5 years I have been involved in about 4-6 count cases in different aspects (inheritance, insurance, family, criminal, ...) and during work with my legal counsels I must say I also think I liked it. Here, by "I think I liked it" I mean, that I have spent many hours crawling though Internet and finding paragraphs that would match my cases, as well as court judgments, that were relevant to us, and lastly discussing those topics with legal adviser. Because of that, I have an idea of starting studying law.
Now, this creates few problems:
My past, current as well as future studies in computer science costs are covered by government (Poland), however starting different degrees like law or management would require me to pay for them. I already have very well paid job (senior java dev) as well as money to fully cover those expenses, however taking both degrees would mostly deplete my savings (I am not counting in money, that I will receive from holiday work and passive income, that is enough to covers my basic needs). Alternative is investing money in something else (more passive income?) that could result in better ROI that next degrees.
Studying full time requires me to limit my work to holidays - I am totally ok with it, however most employers are not, and so this is problem - finding job only on holidays.
My mother has completed 3 different degrees and was sometimes telling me, that she has 3 versions of CV (full/true, chopped off, very basic) with very basic mentioning only single degree, because she believes, that when she is sending full/true CV it scares away recruiters as they perceive her as "overqualified, that will surely leave company in near future for better position". I believe my plan of acquiring 3 degrees would leave me with same problem, but at the same time I simply like learning new things.
I am 24 year old. Assuming, that I will take PhD (4 years) and one of law/management (5 years) and then after completing PhD second of management/law (5 years), then I will be 24 + 4 + 5 = 33 year old with (current) 2 years + 2 years (27 months = 9 years * 3 months - holidays) = only 4 years of professional experience. I believe, that most people with 33 years will have double or triple professional experience than me. It's also worth noting, that this is optimistic calculation, that assumes, that I will every year will be able to find job just for holidays and that I will finish all 3 degrees without any delay.
I am totally ok with starting studying new degree and then dropping it, if I will have feeling, that it it's not what I have been thinking about it. It's also worth to note, that I still like computer science and I do not need/want to leave it. I also don't have to work (passive income) however I really like programming (also in work) so I would like to do it if only I will have opportunity to do so.
Have I omitted some problem, that I should consider? Are there better/other solutions to problems I have listed?